Three years ago, a struggling Red Sox team dumped a big part of their roster — and their payroll — on the Los Angeles Dodgers, shipping Adrian Gonzalez, Carl Crawford, and Josh Beckett to Los Angeles in exchange for a few prospects and a lot of financial relief. The deal freed up the team to reallocate a bunch of that money to free agents a few months later, and after hitting on signings like Shane Victorino, Mike Napoli, Stephen Drew, and Koji Uehara, the team celebrated a World Series title in 2013.

Things have fallen apart again since, however, and last winter’s free agent spending spree looks like a total disaster at this point. Hanley Ramirez and Pablo Sandoval have combined for -1.8 WAR while pulling in $40 million between them, and there’s no way the team can go into 2016 with this same defensive alignment. Ramirez is clearly not an outfielder, and Sandoval has been a bit of disaster at third base this year as well, leading to speculation that one of the two may move to first base next year. And that probably is the path of least resistance, but as rumors percolated of Red Sox-Padres trade discussion before last week’s deadline, I started wondering if there wasn’t an August deal to be made that might actually make sense for both sides.

After all, reports from last winter suggest that Sandoval actually turned down a larger offer from the Padres to sign with the Red Sox. The Padres liked him enough to make him a $100 million offer, and they haven’t found a new long-term answer at 3B in the meantime. I’m sure they’re probably pretty happy to not be on the hook for the deal they offered him a year ago, but it does seem at least somewhat possible that they’d still be interested in having Sandoval on their team, especially if the Red Sox paid down some of his contract. And extra especially when you see that this winter’s free agent crop at third base is led by Juan Uribe, with David Freese and Alberto Callaspo the best alternative options for whatever team doesn’t sign Uribe.

If the Padres really are sticking to their planning in trying to win next year, then they’re going to have to take some shots on buy-low guys like Sandoval, because they don’t have the payroll space to sign a bunch of premium free agents, nor the trade chips to acquire low-salaried impact talent. If the goal is still to win with the core they put together last winter, they’re going to have to be on the winning side of a few upside plays, getting other teams to give them players with some upside in change-of-scenery deals.

As a switch-hitting 3B who still projects as a roughly average player even with his miserable 2015 now in his performance record, buying low on Sandoval isn’t the worst idea in the world. He’s certainly not worth the remaining $75 million he has left on his contract, but there is some potential for him to bounce back and live up to a chunk of that guarantee. So, the question from San Diego’s end may be how they get Sandoval cheap enough to take the plunge.

The easy way to offset most of Sandoval’s salary is to include James Shields in the trade. The Red Sox rotation continues to be a source of consternation, and it’s widely expected that the team will look to outside acquisitions to bolster their starting staff this winter. While Shields results this year haven’t been what the Padres were hoping for when they signed him, his BB/K/GB rates all remain solid, offering some hope for a bounce-back of his own. And because the Padres backloaded his contract, he has $65 million remaining on his deal over the next three years, putting his contract somewhat in line with Sandoval’s deal going forward.

The Padres certainly wouldn’t swap the two straight up, of course; Shields is better and costs less, so while Sandoval is well in the red relative to his deal, Shields is closer to break-even, maybe more like $10 million to the negative side of things. If the Red Sox wanted the Padres to think about a Shields/Sandoval swap, they’d have to sweeten the pot. But they have a lot of guys who could interest the Padres, especially if they’re looking to upgrade for 2016.

For instance, Jackie Bradley Jr would give the Padres a legitimate Major League center fielder, something that they just haven’t had this year; with both Justin Upton and Will Venable leaving as free agents, most likely, the team almost certainly will slide Wil Myers back to a corner spot where he belongs, opening up center field for a better defender. Bradley continues to hit well enough in Triple-A to suggest that he has enough offensive upside to be worth taking a shot on, and his defense is good enough that he doesn’t have to hit a ton in order to be valuable; even something like Juan Lagares‘ offensive levels (career 84 wRC+) would be good enough to let him hold down an everyday CF job.

Bradley himself doesn’t offset the value difference between Sandoval and Shields, but if Boston also included Deven Marrero — a similar kind of prospect, a glove-first SS who probably won’t hit but is probably better than anything San Diego has in the pipeline — you might start to get A.J. Preller to start thinking about the swap. Turning one pitcher into three position players who could potentially step right into the Padres line-up is the kind of deal they’ll need to make if they want to try and win next year. At the least, Bradley and Marrero would close the value gap enough to make the cash side of the equation pretty minimal; maybe the Red Sox kick in an extra $5 million or something, but it’s in the range of reasonable for both sides at that point.

Because minor leaguers can be traded in August without needing to clear waivers by using the player-to-be-named-later tactic, and Shields and Sandoval would both clear waivers without any problem, this is the kind of trade that teams can still make in August, and the lack of urgency might be why talks didn’t lead to a deal before the deadline. With players like this, the deadline doesn’t really apply.

Most likely, something like this won’t happen, as it’s tough for teams to sell low on guys who were touted as big acquisitions less than a year ago. This would take some pride-swallowing on both sides, and the Red Sox would have to be willing to move a couple of depth pieces simply for the right to move one negative-value asset for another one. But if they could ship Sandoval off to San Diego, they could move Ramirez back to third base — where he’s previously been below average but not the disaster he was in left field — and add a potentially solid starting pitcher to their rotation in the process.

But if we’re looking for an August trade beyond just Marlon Byrd or Chase Utley for some low level prospect in a salary dump, this is the kind of deal we could still see happen.

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It would have to be the Dodgers. Boston has a worse record than the Yankees, so Boston’s claim would take precedence.

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3 years ago

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TKDC

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The way Dave frames it, Boston would have to pass, or else SD just dumps him on the them and they’d have to pay down Sandoval fully to his current value.

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So, you don’t want to risk Shields passing by the Sox and being claimed by another team. So the Sox claim him. If the Sox and Padres can’t agree to a deal, then the Sox are stuck with Shields’ full contract. What’s the problem with that from the Sox’ perspective?

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And if the Padres aren’t happy with giving Shields away for free, they can revoke the waivers.

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3 years ago

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TKDC

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The problem is that as Dave puts it, Shields has negative $10 million in value that would offset some of the money Boston would have to give in order to rid themselves of Sandoval. Also, they’d be taking on a few million dollars for 2015 with absolutely no benefit, as they are not close to contending.

Boston would not claim Shields. If another team did, the Padres should let him go, and then if they want Sandoval (who would obviously pass through waivers) they can work out an independent deal, but Boston would be on the hook for more than Dave theorizes here.

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I’ll admit I hadn’t looked at Shields’ contract before posting above, and I haven’t done any analysis on what his market value should be. But my point is this:

James Shields is a good starting pitcher, has some of the best peripheral numbers of his career this year, and he only has 3 more guaranteed years. If the numbers work out that his remaining contract *is* close to market value, a team like the Red Sox (who have deep pockets, a need for good starters, and an understanding of advanced stats) should be willing to take on his full contract.

And if his remaining contract is *not* close to market value, there’s no problem because then no team will claim him and he’ll pass through waivers.

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3 years ago

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TKDC

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Shields is worth more to a team in contention this year than he is to Boston. LA for instance.

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3 years ago

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Bono

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Shields doesn’t have to be claimed – if he clears waivers then the trade can go through as imagined. And I’m with Dave in thinking the Yankees would steer clear. There are better pitchers available than Shields after the season – if they’re going to take on a multi-year deal for a started it would be a top tier one, not a declining Shields. I think that holds true for the Dodgers too. Neither team would really benefit from Shields for a few starts and then the playoffs.